426288

Tetrabutylammonium bromide

ACS reagent, ≥98.0%

• Synonym(s): N,N,N-tributyl-1-butanaminium bromide, TBAB, TBABr, tetra-n-butylammonium bromide
• Linear Formula: (CH₃CH₂CH₂CH₂)₄N(Br)
• CAS Number: 1643-19-2
• Molecular Weight: 322.37
• Beilstein: 3570983
• EC Number: 216-699-2
• MDL number: MFCD00011633
• UNSPSC Code: 12352100
• PubChem Substance ID: 24866693
• NACRES: NA.21
• Assay: ≥98.0%
• grade: ACS reagent
• form: solid

Properties

• grade: ACS reagent
• Quality Level: 200
• Assay: ≥98.0%
• form: solid
• greener alternative product characteristics: Catalysis; Learn more about the Principles of Green Chemistry.
• sustainability: Greener Alternative Product
• impurities: ≤0.5% tributylamine hydrobromide; ≤0.5% tributylamine
• mp: 102-106 °C (lit.)
• functional group: amine
• greener alternative category: Aligned
• SMILES string: [Br-].CCCC[N+](CCCC)(CCCC)CCCC
• InChI: 1S/C16H36N.BrH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1
• InChI key: JRMUNVKIHCOMHV-UHFFFAOYSA-M

Description

General description

Tetrabutylammonium bromide (TBAB) is a quaternary ammonium compound.[1] It is the most widely used phase transfer catalyst.[2] Its interfacial properties have been studied in case of hydroxide initiated reactions. This may be applied in understanding the mechanism of phase transfer reactions.[1] TBAB is reported to decrease retention time and remove peak tailing by acting as an ion pair reagent during the chromatographic analysis of quaternary ammonium compounds.[2] In the molten state TBAB behaves like an ionic liquid which is a promising green alternative to organic solvents in organic synthesis.[3][4] Its molar heat capacity, entropy and free energy function have been determined.[5]

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Application

Tetrabutylammonium bromide (TBAB) may be used in the molten state in the following processes:

• Synthesis of (2S)-5-(3-phenyl-2-phthalimidylpropanoylamino)isophthalic acid.[6]
• Synthesis of alkyl-substituted pyrroles in the absence of catalyst and organic solvent.[7]
• Synthesis of dithioacetals from acetals by transthioacetalisation in a solvent free environment.[8]
• Synthesis of polyamides (PAs) by the polymerization of terephthalic acid and diisocyanates.[4]
• Catalyze the addition of thiols to conjugated alkenes.[9]
• Dehydrochlorination of poly(vinyl chloride).[10]

Used with phosphorus pentoxide for greener deoxybromination.

Used with phosphorus pentoxide for greener deoxybromination.
Process for Producing Halogenated Heteroaryl Compounds

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Warning
• Hazard Statements: H302,H315,H319,H361fd,H412
• Precautionary Statements: P202 - P273 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves